U.S. patent application number 12/680377 was filed with the patent office on 2010-10-07 for method of producing benzoxazinone-based compound.
Invention is credited to Keizo Kimura, Takashi Kitagawa, Osamu Uchida.
Application Number | 20100256362 12/680377 |
Document ID | / |
Family ID | 40511587 |
Filed Date | 2010-10-07 |
United States Patent
Application |
20100256362 |
Kind Code |
A1 |
Kimura; Keizo ; et
al. |
October 7, 2010 |
METHOD OF PRODUCING BENZOXAZINONE-BASED COMPOUND
Abstract
A method of producing a compound represented by Formula (I),
which comprises a step A of reacting an anthranilic acid compound
with a carboxylic halide in the absence of a base, but does not
comprise a step of isolating of an amide intermediate compound
represented by Formula (II): ##STR00001## wherein R.sub.1
represents a substituent; n.sub.1 is an integer of 0 to 4; R.sub.2
represents an n.sub.2-valent substituent or a linking group; and
n.sub.2 is an integer of 1 to 4.
Inventors: |
Kimura; Keizo; (Kanagawa,
JP) ; Kitagawa; Takashi; (Kanagawa, JP) ;
Uchida; Osamu; (Kanagawa, JP) |
Correspondence
Address: |
BUCHANAN, INGERSOLL & ROONEY PC
POST OFFICE BOX 1404
ALEXANDRIA
VA
22313-1404
US
|
Family ID: |
40511587 |
Appl. No.: |
12/680377 |
Filed: |
September 25, 2008 |
PCT Filed: |
September 25, 2008 |
PCT NO: |
PCT/JP2008/067879 |
371 Date: |
March 26, 2010 |
Current U.S.
Class: |
544/73 ;
544/92 |
Current CPC
Class: |
C07D 265/36 20130101;
C07D 413/04 20130101; C07D 265/18 20130101; C07D 413/14 20130101;
C07D 265/12 20130101 |
Class at
Publication: |
544/73 ;
544/92 |
International
Class: |
C07D 413/10 20060101
C07D413/10; C07D 265/16 20060101 C07D265/16 |
Foreign Application Data
Date |
Code |
Application Number |
Sep 27, 2007 |
JP |
2007-252729 |
Mar 31, 2008 |
JP |
2008-091834 |
Claims
1. A method of producing a compound represented by Formula (I),
which comprises: a step A of feasting allowing an anthranilic acid
compound to react with a carboxylic halide in the absence of a
base, but does not comprise any, step of isolating an amide
intermediate compound represented by Formula (II): ##STR00007##
wherein R.sub.1 represents a substituent; n.sub.1 is an integer of
0 to 4; R.sub.2 represents an n.sub.2-valent substituent or a
linking group; and n.sub.2 is an integer of 1 to 4.
2. The method according to claim 1, wherein at least one kind of a
reaction solvent is used in the step A, and the said at least one
kind of a reaction solvent has a donor number of 10 or more.
3. The method according to claim 1, wherein no protic solvent is
used in the step A.
4. The method according to claim 1, wherein the temperature of the
step A is 50.degree. C. or lower.
5. The method according to claim 1, wherein the temperature of the
step A is -15.degree. C. or more and 20.degree. C. or lower.
6. The method according to claim 1, wherein the carboxylic halide
is prepared by acid halogenation of a carboxylic acid compound and
used as it is without isolation after preparation.
7. The method according to claim 2, wherein no protic solvent is
used in the step A.
Description
TECHNICAL FIELD
[0001] The present invention relates to a method of producing an
ultraviolet absorbent for thermoplastic polymers, more
specifically, to an inexpensive and effective method of producing a
high-purity benzoxazinone-based compound, an ultraviolet absorbing
material useful in optical film application.
BACKGROUND ART
[0002] Benzotriazole-based compounds, benzophenone-based compounds,
salicylic acid-based compounds, triazine-based compounds and the
like have been used as the ultraviolet absorbents for thermoplastic
polymers. These ultraviolet absorbents generally had problems such
as insufficient ultraviolet cut rate, insufficient heat resistance,
easy color development, and insufficient fastness.
[0003] Benzoxazinone compounds have been proposed as the
ultraviolet absorbents solving the problems above (see, e.g.,
JP-B-62-5944 ("JP-B" means examined Japanese patent publication)
and JP-B-62-31027). A method of producing such a compound by using
isatoic acid anhydride as the raw material is already known, but
the method is still not satisfactory in that the raw material is
expensive (see, e.g., U.S. Pat. No. 3,989,698 or JP-A-62-11744
("JP-A" means unexamined published Japanese patent
application)).
[0004] Also known is a method of using anthranilic acid as the raw
material, but the method, which is a two-step process via an amide
intermediate, was complicated in operation and lower in
productivity, demanding further improvement (see, e.g., U.S. Pat.
No. 3,408,326, JP-A-58-194854 and JP-A-61-291575).
[0005] Processes of producing it continuously from anthranilic acid
without isolation of the amide intermediate to solve the problems
above are also known (see, e.g., JP-A-2000-264879), but addition of
an inorganic alkali as a base, such as sodium carbonate, for
control of by-product generation in the amide
intermediate-generating step caused a problem of sodium
contamination in the final isolated product and deterioration in
quality.
DISCLOSURE OF INVENTION
[0006] According to the present invention, there is provided the
following means:
[0007] [1] A method of producing a compound represented by Formula
(I), which comprises a step A of reacting an anthranilic acid
compound with a carboxylic halide in the absence of a base, but
does not comprise a step of isolating an amide intermediate
compound represented by Formula (II):
##STR00002##
[0008] wherein R.sub.1 represents a substituent; n.sub.1 is an
integer of 0 to 4; R.sub.2 represents an n.sub.2-valent substituent
or a linking group; and n.sub.2 is an integer of 1 to 4;
[0009] [2] The method described in the above item [1], wherein at
least one kind of reaction solvent used in the step A has a donor
number of 10 or more;
[0010] [3] The method described in the above item [1] or [2],
wherein no protic solvent is used in the step A;
[0011] [4] The method described in any one of the above items [1]
to [3], wherein the temperature of the step A is 50.degree. C. or
lower; and
[0012] [5] The method described in any one of the above items [1]
to [4], wherein the carboxylic halide is prepared by acid
halogenation of a carboxylic acid compound and used as it is
without isolation after preparation.
[0013] Other and further features and advantages of the invention
will appear more fully from the following description.
BEST MODE FOR CARRYING OUT INVENTION
[0014] The present invention is explained in detail below.
[0015] In the present specification, the aliphatic group means an
alkyl group, a substituted alkyl group, an alkenyl group, a
substituted alkenyl group, an alkynyl group, a substituted alkynyl
group, an aralkyl group, and a substituted aralkyl group. The
aforementioned alkyl group may have a branch or may form a ring
(i.e. a cycloalkyl group). The alkyl group preferably has 1 to 20
carbon atoms, and more preferably 1 to 18 carbon atoms. The alkyl
moiety in the aforementioned substituted alkyl group is the same as
the above mentioned alkyl group. The aforementioned alkenyl group
may have a branch or may form a ring (i.e. a cycloalkenyl group).
The alkenyl group has preferably 2 to 20 carbon atoms, and more
preferably 2 to 18 carbon atoms. The alkenyl moiety in the
aforementioned substituted alkenyl group is the same as the above
mentioned alkenyl group. The aforementioned alkynyl group may have
a branch or may form a ring (i.e. a cycloalkynyl group). The
alkynyl group has preferably 2 to 20 carbon atoms, and more
preferably 2 to 18 carbon atoms. The alkynyl moiety in the
aforementioned substituted alkynyl group is the same as the above
mentioned alkynyl group. The alkyl moiety in the aforementioned
aralkyl group and substituted aralkyl group is the same as the
above mentioned alkyl group. The aryl moiety in the aforementioned
aralkyl group and substituted aralkyl group is the same as the aryl
group mentioned below.
[0016] Specific examples of the substituent in the substituted
alkyl group, the substituted alkenyl group, the substituted alkynyl
group, and the alkyl moiety in the substituted aralkyl group
include: a halogen atom (e.g. a chlorine atom, a bromine atom, or
an iodine atom); an alkyl group which represents a substituted or
unsubstituted linear, branched, or cyclic alkyl group, and which
includes an alkyl group (preferably an alkyl group having 1 to 30
carbon atoms, e.g. a methyl group, an ethyl group, an n-propyl
group, an isopropyl group, a t-butyl group, an n-octyl group, an
eicosyl group, a 2-chloroethyl group, a 2-cyanoethyl group, or a
2-ethylhexyl group), a cycloalkyl group (preferably a substituted
or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, e.g.
a cyclohexyl group, a cyclopentyl group, or a 4-n-dodecylcyclohexyl
group), a bicycloalkyl group (preferably a substituted or
unsubstituted bicycloalkyl group having 5 to 30 carbon atoms, i.e.
a monovalent group obtained by removing one hydrogen atom from a
bicycloalkane having 5 to 30 carbon atoms, e.g. a
bicyclo[1,2,2]heptan-2-yl group or a bicyclo[2,2,2]octan-3-yl
group), and a tricyclo or higher structure having three or more
ring structures; and an alkyl group in a substituent explained
below (e.g. an alkyl group in an alkylthio group) represents such
an alkyl group of the above concept]; an alkenyl group which
represents a substituted or unsubstituted linear, branched, or
cyclic alkenyl group, and which includes an alkenyl group
(preferably a substituted or unsubstituted alkenyl group having 2
to 30 carbon atoms, e.g. a vinyl group, an allyl group, a prenyl
group, a geranyl group, or an oleyl group), a cycloalkenyl group
(preferably a substituted or unsubstituted cycloalkenyl group
having 3 to 30 carbon atoms, i.e. a monovalent group obtained by
removing one hydrogen atom from a cycloalkene having 3 to 30 carbon
atoms, e.g. a 2-cyclopenten-1-yl group or a 2-cyclohexen-1-yl
group), and a bicycloalkenyl group (which represents a substituted
or unsubstituted bicycloalkenyl group, preferably a substituted or
unsubstituted bicycloalkenyl group having 5 to 30 carbon atoms,
i.e. a monovalent group obtained by removing one hydrogen atom from
a bicycloalkene having one double bond, e.g. a
bicyclo[2,2,1]hept-2-en-1-yl group or a bicyclo[2,2,2]oct-2-en-4-yl
group)]; an alkynyl group (preferably a substituted or
unsubstituted alkynyl group having 2 to 30 carbon atoms, e.g. an
ethynyl group, a propargyl group, or a trimethylsilylethynyl
group); an aryl group (preferably a substituted or unsubstituted
aryl group having 6 to 30 carbon atoms, e.g. a phenyl group, a
p-tolyl group, a naphthyl group, an m-chlorophenyl group, or an
o-hexadecanoylaminophenyl group); a heterocyclic group (preferably
a monovalent group obtained by removing one hydrogen atom from a
substituted or unsubstituted 5- or 6-membered aromatic or
nonaromatic heterocyclic compound; more preferably a 5- or
6-membered aromatic heterocyclic group having 3 to 30 carbon atoms,
e.g. a 2-furyl group, a 2-thienyl group, a 2-pyrimidinyl group, a
2-benzothiazolyl group); a cyano group; a hydroxy group; a nitro
group; a carboxyl group; an alkoxy group (preferably a substituted
or unsubstituted alkoxy group having 1 to 30 carbon atoms, e.g. a
methoxy group, an ethoxy group, an isopropoxy group, a t-butoxy
group, an n-octyloxy group, or a 2-methoxyethoxy group); an aryloxy
group (preferably a substituted or unsubstituted aryloxy group
having 6 to 30 carbon atoms, e.g. a phenoxy group, a
2-methylphenoxy group, a 4-t-butylphenoxy group, a 3-nitrophenoxy
group, or a 2-tetradecanoylaminophenoxy group); a silyloxy group
(preferably a silyloxy group having 3 to 20 carbon atoms, e.g. a
trimethylsilyloxy group or a t-butyldimethylsilyloxy group); a
heterocyclic oxy group (preferably a substituted or unsubstituted
heterocyclic oxy group having 2 to 30 carbon atoms, e.g. a
1-phenyltetrazol-5-oxy group or a 2-tetrahydropyranyloxy group); an
acyloxy group (preferably a formyloxy group, a substituted or
unsubstituted alkylcarbonyloxy group having 2 to 30 carbon atoms,
or a substituted or unsubstituted arylcarbonyloxy group having 7 to
30 carbon atoms, e.g. a formyloxy group, an acetyloxy group, a
pivaloyloxy group, a stearoyloxy group, a benzoyloxy group, or a
p-methoxyphenylcarbonyloxy group); a carbamoyloxy group (preferably
a substituted or unsubstituted carbamoyloxy group having 1 to 30
carbon atoms, e.g. an N,N-dimethylcarbamoyloxy group, an
N,N-diethylcarbamoyloxy group, a morpholinocarbonyloxy group, an
N,N-di-n-octylaminocarbonyloxy group, or an N-n-octylcarbamoyloxy
group); an alkoxycarbonyloxy group (preferably a substituted or
unsubstituted alkoxycarbonyloxy group having 2 to 30 carbon atoms,
e.g. a methoxycarbonyloxy group, an ethoxycarbonyloxy group, a
t-butoxycarbonyloxy group, or an n-octylcarbonyloxy group); an
aryloxycarbonyloxy group (preferably a substituted or unsubstituted
aryloxycarbonyloxy group having 7 to 30 carbon atoms, e.g. a
phenoxycarbonyloxy group, a p-methoxyphenoxycarbonyloxy group, or a
p-n-hexadecyloxyphenoxycarbonyloxy group); an amino group
(preferably an amino group, a substituted or unsubstituted
alkylamino group having 1 to 30 carbon atoms, or a substituted or
unsubstituted anilino group having 6 to 30 carbon atoms, e.g. an
amino group, a methylamino group, a dimethylamino group, an anilino
group, an N-methyl-anilino group, or a diphenylamino group); an
acylamino group (preferably a formylamino group, a substituted or
unsubstituted alkylcarbonylamino group having 1 to 30 carbon atoms,
or a substituted or unsubstituted arylcarbonylamino group having 6
to 30 carbon atoms, e.g. a formylamino group, an acetylamino group,
a pivaloylamino group, a lauroylamino group, a benzoylamino group,
or a 3,4,5-tri-n-octyloxyphenylcarbonylamino group); an
aminocarbonylamino group (preferably a substituted or unsubstituted
aminocarbonylamino group having 1 to 30 carbon atoms, e.g. a
carbamoylamino group, an N,N-dimethylaminocarbonylamino group, an
N,N-diethylaminocarbonylamino group, or a morpholinocarbonylamino
group); an alkoxycarbonylamino group (preferably a substituted or
unsubstituted alkoxycarbonylamino group having 2 to 30 carbon
atoms, e.g. a methoxycarbonylamino group, an ethoxycarbonylamino
group, a t-butoxycarbonylamino group, an
n-octadecyloxycarbonylamino group, or an
N-methyl-methoxycarbonylamino group); an aryloxycarbonylamino group
(preferably a substituted or unsubstituted aryloxycarbonylamino
group having 7 to 30 carbon atoms, e.g. a phenoxycarbonylamino
group, a p-chlorophenoxycarbonylamino group, or an
m-n-octyloxyphenoxycarbonylamino group); a sulfamoylamino group
(preferably a substituted or unsubstituted sulfamoylamino group
having 0 to 30 carbon atoms, e.g. a sulfamoylamino group, an
N,N-dimethylaminosulfonylamino group, or an
N-n-octylaminosulfonylamino group); an alkyl- or aryl-sulfonylamino
group (preferably a substituted or unsubstituted alkylsulfonylamino
group having 1 to 30 carbon atoms, or a substituted or
unsubstituted arylsulfonylamino group having 6 to 30 carbon atoms,
e.g. a methylsulfonylamino group, a butylsulfonylamino group, a
phenylsulfonylamino group, a 2,3,5-trichlorophenylsulfonylamino
group, or a p-methylphenylsulfonylamino group); a mercapto group;
an alkylthio group (preferably a substituted or unsubstituted
alkylthio group having 1 to 30 carbon atoms, e.g. a methylthio
group, an ethylthio group, or an n-hexadecylthio group); an
arylthio group (preferably a substituted or unsubstituted arylthio
group having 6 to 30 carbon atoms, e.g. a phenylthio group, a
p-chlorophenylthio group, or an m-methoxyphenylthio group); a
heterocyclic thio group (preferably a substituted or unsubstituted
heterocyclic thio group having 2 to 30 carbon atoms, e.g. a
2-benzothiazolylthio group or a 1-phenyltetrazol-5-ylthio group); a
sulfamoyl group (preferably a substituted or unsubstituted
sulfamoyl group having 0 to 30 carbon atoms, e.g. an
N-ethylsulfamoyl group, an N-(3-dodecyloxypropyl)sulfamoyl group,
an N,N-dimethylsulfamoyl group, an N-acetylsulfamoyl group, an
N-benzoylsulfamoyl group, or an N-(N'-phenylcarbamoyl)sulfamoyl
group); a sulfo group; an alkyl- or aryl-sulfonyl group (preferably
a substituted or unsubstituted alkylsulfonyl group having 1 to 30
carbon atoms, or a substituted or unsubstituted arylsulfinyl group
having 6 to 30 carbon atoms, e.g. a methylsulfonyl group, an
ethylsulfinyl group, a phenylsulfinyl group, or a
p-methylphenylsulfinyl group); an alkyl- or aryl-sulfonyl group
(preferably a substituted or unsubstituted alkylsulfonyl group
having 1 to 30 carbon atoms, or a substituted or unsubstituted
arylsulfonyl group having 6 to 30 carbon atoms, e.g. a
methylsulfonyl group, an ethylsulfonyl group, a phenylsulfonyl
group, or a p-methylphenylsulfonyl group); an acyl group
(preferably a formyl group, a substituted or unsubstituted
alkylcarbonyl group having 2 to 30 carbon atoms, a substituted or
unsubstituted arylcarbonyl group having 7 to 30 carbon atoms, or a
substituted or unsubstituted heterocyclic carbonyl group having 4
to 30 carbon atoms and being bonded to said carbonyl group through
a carbon atom, e.g. an acetyl group, a pivaloyl group, a
2-chloroacetyl group, a stearoyl group, a benzoyl group, a
p-n-octyloxyphenylcarbonyl group, a 2-pyridylcarbonyl group, or a
2-furylcarbonyl group); an aryloxycarbonyl group (preferably a
substituted or unsubstituted aryloxycarbonyl group having 7 to 30
carbon atoms, e.g. a phenoxycarbonyl group, an
o-chlorophenoxycarbonyl group, an m-nitrophenoxycarbonyl group, or
a p-t-butylphenoxycarbonyl group); an alkoxycarbonyl group
(preferably a substituted or unsubstituted alkoxycarbonyl group
having 2 to 30 carbon atoms, e.g. a methoxycarbonyl group, an
ethoxycarbonyl group, a t-butoxycarbonyl group, or an
n-octadecyloxycarbonyl group); a carbamoyl group (preferably a
substituted or unsubstituted carbamoyl group having 1 to 30 carbon
atoms, e.g. a carbamoyl group, an N-methylcarbamoyl group, an
N,N-dimethylcarbamoyl group, an N,N-di-n-octylcarbamoyl group, or
an N-(methylsulfonyl)carbamoyl group); an aryl- or heterocyclic-azo
group (preferably a substituted or unsubstituted aryl azo group
having 6 to 30 carbon atoms, or a substituted or unsubstituted
heterocyclic azo group having 3 to 30 carbon atoms, e.g. a
phenylazo group, a p-chlorophenylazo group, or a
5-ethylthio-1,3,4-thiadiazol-2-ylazo group); an imido group
(preferably an N-succinimido group or an N-phthalimido group); a
phosphino group (preferably a substituted or unsubstituted
phosphino group having 2 to 30 carbon atoms, e.g. a
dimethylphosphino group, a diphenylphosphino group, or a
methylphenoxyphosphino group); a phosphinyl group (preferably a
substituted or unsubstituted phosphinyl group having 2 to 30 carbon
atoms, e.g. a phosphinyl group, a dioctyloxyphosphinyl group, or a
diethoxyphosphinyl group); a phosphinyloxy group (preferably a
substituted or unsubstituted phosphinyloxy group having 2 to 30
carbon atoms, e.g. a diphenoxyphosphinyloxy group or a
dioctyloxyphosphinyloxy group); a phosphinylamino group (preferably
a substituted or unsubstituted phosphinylamino group having 2 to 30
carbon atoms, e.g. a dimethoxyphosphinylamino group or a
dimethylaminophosphinylamino group); and a silyl group (preferably
a substituted or unsubstituted silyl group having 3 to 30 carbon
atoms, e.g. a trimethylsilyl group, a t-butyldimethylsilyl group,
or a phenyldimethylsilyl group).
[0017] Among the above functional groups, those having a hydrogen
atom may further be substituted with any of the above groups at the
position from which the hydrogen atom is removed. Examples of such
a functional group include an alkylcarbonylaminosulfonyl group, an
arylcarbonylaminosulfonyl group, an alkylsulfonylaminocarbonyl
group, and an arylsulfonylaminocarbonyl group. Specific examples of
these groups include a methylsulfonylaminocarbonyl, a
p-methylphenylsulfonylaminocarbonyl, an acetylaminosulfonyl, and a
benzoylaminosulfonyl group.
[0018] Examples of the substituent on the aryl moiety of the
substituted aralkyl group include substituents of the following
substituted aryl groups.
[0019] The aromatic group in this specification means an aryl group
or a substituted aryl group. Further, these aromatic groups may be
condensed with aliphatic rings, other aromatic rings or hetero
rings. The number of carbon atoms of the aromatic group is
preferably 6 to 40, more preferably 6 to 30, and still more
preferably 6 to 20. Among these groups, the aryl group is
preferably phenyl or naphthyl, and particularly preferably
phenyl.
[0020] The aryl moiety of the substituted aryl group is the same as
the above aryl group. Examples of the substituent of the
substituted aryl group include those given above as the
substituents of the substituted alkyl group, the substituted
alkenyl group, the substituted alkynyl group, and the alkyl moiety
of the substituted aralkyl group.
[0021] In the present specification, a heterocyclic group
preferably contains a 5- or 6-membered saturated or unsaturated
heterocycle. Such a heterocycle may be condensed with an aliphatic
ring, an aromatic ring, or another heterocycle. Examples of the
heteroatom in the heterocycle include boron (B), nitrogen (N),
oxygen (O), sulfur (S), selenium (Se) and Tellurium (Te). As a
heteroatom, nitrogen (N), oxygen (O) or sulfur (S) are preferable.
The heterocycle preferably has a free monovalent carbon atom (the
heterocyclic group binds at the carbon atom). The heterocyclic
group has preferably 1 to 40 carbon atoms, more preferably 1 to 30
carbon atoms, and further more preferably 1 to 20 carbon atoms.
Examples of the saturated heterocycle include a pyrrolidine ring, a
morpholine ring, 2-bora-1,3-dioxolan ring, and 1,3-thiazolidine
ring. Examples of the unsaturated heterocycle include an imidazole
ring, a thiazole ring, a benzothiazole ring, a benzoxazole ring, a
benzotriazole ring, a benzoselenazole ring, a pyridine ring, a
pyrimidine ring, and a quinoline ring. The heterocyclic group may
have a substituent or substituents. Examples of the substituent
include the substituents listed above as the substituents for the
substituted alkyl group, the substituted alkenyl group, the
substituted alkynyl group, and the alkyl moiety of the substituted
aralkyl group.
[0022] Next, the compounds represented by formulae (I) to (II) are
explained below. In formulae (I) to (II), R.sub.1 represents a
substituent. Examples of the substituent on R.sub.1 include the
substituents listed above for the substituted alkyl group, the
substituted alkenyl group, the substituted alkynyl group, and the
alkyl moiety of the substituted aralkyl group.
[0023] Preferred examples of R.sub.1 include a halogen atom, an
alkyl group, an alkenyl group, an alkynyl group, an aryl group, a
cyano group, a hydroxy group, a nitro group, a carboxyl group, an
alkoxy group, an aryloxy group, a silyloxy group, a heterocyclic
oxy group, an acyloxy group, a carbamoyloxy group, an
alkoxycarbonyloxy group, an aryloxycarbonyloxy group, an amino
group, an acylamino group, an aminocarbonylamino group, an
alkoxycarbonylamino group, an aryloxycarbonylamino group, a
sulfamoylamino group, an alkylsulfonylamino group, an
arylsulfonylamino group, a mercapto group, an alkyl thio group, an
aryl thio group, a heterocyclic thio group, a sulfamoyl group, a
sulfo group, an alkyl sulfinyl group, an aryl sulfinyl group, an
alkyl sulfonyl group, an aryl sulfonyl group, an acyl group, an
aryloxycarbonyl group, an alkoxycarbonyl group, a carbamoyl group,
an imido group, a phosphino group, a phosphinyl group, a
phosphinyloxy group, a phosphinylamino group, and a silyl group.
More preferred examples of R.sub.1 include a halogen atom, an alkyl
group, an aryl group, a cyano group, a hydroxy group, a nitro
group, a carboxyl group, an alkoxy group, an aryloxy group, a
silyloxy group, a heterocyclic oxy group, an acyloxy group, a
carbamoyloxy group, an amino group, an acylamino group, an
aminocarbonylamino group, an alkoxycarbonylamino group, an
aryloxycarbonylamino group, a sulfamoylamino group, an
alkylsulfonylamino group, an arylsulfonylamino group, a mercapto
group, an alkyl thio group, an aryl thio group, a heterocyclic thio
group, a sulfamoyl group, a sulfo group, an alkyl sulfinyl group,
an aryl sulfinyl group, an alkyl sulfonyl group, an aryl sulfonyl
group, a carbamoyl group, an imido group, a phosphino group, a
phosphinyl group, a phosphinyloxy group, a phosphinylamino group
and a silyl group. Furthermore preferred examples of R.sub.1
include a halogen atom, an alkyl group, an aryl group, a hydroxy
group, an alkoxy group, an aryloxy group, an amino group, a
mercapto group, an alkyl thio group, an aryl thio group, a
sulfamoyl group, a sulfo group, an alkyl sulfinyl group, an aryl
sulfinyl group, an alkyl sulfonyl group and an aryl sulfonyl group.
Furthermore preferred examples of R.sub.1 include a halogen atom,
an alkyl group, an aryl group, an alkoxy group, an aryloxy group,
an alkyl thio group and an aryl thio group. Furthermore preferred
examples of R.sub.1 include a halogen atom, an alkyl group having 1
to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, an
alkoxy group having 1 to 20 carbon atoms, an aryloxy group having 6
to 20 carbon atoms, an alkyl thio group having 1 to 20 carbon atoms
and an aryl thio group having 6 to 20 carbon atoms. Furthermore
preferred examples of R.sub.1 include a chlorine atom, a fluorine
atom, a bromine atom, an alkyl group having 1 to 8 carbon atoms, an
aryl group having 6 to 10 carbon atoms, an alkoxy group having 1 to
8 carbon atoms, an aryloxy group having 6 to 10 carbon atoms, an
alkyl thio group having 1 to 8 carbon atoms and an aryl thio group
having 6 to 10 carbon atoms. Furthermore preferred examples of
R.sub.1 include a chlorine atom, a fluorine atom, an alkyl group
having 1 to 4 carbon atoms and an alkoxy group having 1 to 4 carbon
atoms.
[0024] n.sub.1 is preferably 0 to 3, more preferably 0 to 2, still
more preferably 0 or 1, and most preferably 0, i.e., the benzene
ring has no substituent.
[0025] R.sub.2 represents an n.sub.2-valent substituent or a
linking group, and examples of the substituent include substituents
similar to those on the alkyl units in the substituted alkyl
groups, substituted alkenyl groups, substituted alkynyl groups and
substituted aralkyl groups described above. The linking group is a
substituent having one or more additional binding sites.
[0026] R.sub.2 preferably represents an aliphatic group, an
aromatic group, a heterocyclic group, or a linking group thereof
having another binding site; more preferably an alkyl group, an
alkenyl group, an alkynyl group, an aryl group, a heterocyclic
group of N, O, or S and carbon atoms, or a bivalent to tetravalent
linking group thereof; still more preferably, an alkyl group, an
alkenyl group, an aryl group, a heterocyclic group of N, O, or S
and carbon atoms, or a bivalent to trivalent linking group thereof;
still more preferably an alkyl group having 1 to 20 carbon atoms,
an alkenyl group having 2 to 20 carbon atoms, an aryl group having
6 to 20 carbon atoms, a five- or six-membered heterocyclic group of
N, O, or S and carbon atoms, or a bivalent or trivalent linking
group thereof; still more preferably an alkyl group having 1 to 8
carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an aryl
group having 6 to 12 carbon atoms, a five- or six-membered
heterocyclic group of N, O, or S and carbon atoms, or a bivalent to
trivalent linking group thereof; still more preferably, an alkyl
group having 1 to 8 carbon atoms, an aryl group having 6 to 12
carbon atoms, a five- or six-membered heterocyclic group of N, O,
or S and carbon atoms, or a bivalent to trivalent linking group
thereof; still more preferably, methyl, ethyl, propyl, butyl,
isopropyl, 2-butyl, benzyl, phenyl, 2-naphthyl, pyrrol-2-yl,
thiophen-2-yl, indol-1-yl, indol-2-yl, benzofuran-2-yl,
benzothiophen-2-yl, ethylene, trimethylene, 1,2-propylene,
tetramethylene, 1,2-phenylene, 1,3-phenylene, 1,4-phenylene,
2,6-naphthylene, furan-2,5-yl, thiophene-2,5-yl, or
benzene-1,3,5-yl; still more preferably, methyl, ethyl, benzyl,
phenyl, pyrrol-2-yl, thiophen-2-yl, indol-1-yl, indol-2-yl,
benzothiophen-2-yl, ethylene, trimethylene, 1,3-phenylene,
1,4-phenylene, pyrrole-2,5-yl, thiophene-2,5-yl, or
benzene-1,3,5-yl; still more preferably ethylene, trimethylene,
1,3-phenylene, 1,4-phenylene, pyrrole-2,5-yl, thiophene-2,5-yl, or
benzene-1,3,5-yl; and most preferably, 1,4-phenylene.
[0027] n.sub.2 is preferably 1 to 3, more preferably 2 to 3, and
most preferably 2.
[0028] Next, specific examples of the compounds represented by
formula (I) are shown below. However, the present invention should
not be construed as being limited to these compounds.
##STR00003## ##STR00004## ##STR00005## ##STR00006##
[0029] Hereinafter, the method of producing the compound
represented by Formula (I) according to the present invention will
be described. The method of producing the compound represented by
Formula (I) according to the present invention includes a step A of
reacting an anthranilic acid compound with a carboxylic halide in
the absence of base. The amide intermediate is formed in the step
A. Also in the present invention, the amide intermediate prepared
in the step A is converted into a benzoxazinone skeleton-containing
compound by dehydration condensation in step B, to give the
compound represented by Formula (I). In this case, the reaction
mixture including the amide intermediate prepared in Step A is
preferably subjected to Step B as it is.
[0030] The raw material anthranilic acid compound for use may be a
substituted or unsubstituted anthranilic acid. The substituted
anthranilic acid is, for example, a compound of which hydrogen
atoms on the anthranilic acid benzene ring are replaced with
n.sub.1 pieces of substituents R.sub.1, wherein, R.sub.1 represents
a substituent and n.sub.1 is an integer of 0 to 4. R.sub.1 and
n.sub.1 are respectively the same as those in Formula (I) above,
and the favorable ranges are also the same.
[0031] The raw material carboxylic halide is represented by
R.sub.2(--COX).sub.n2. In the formula, R.sub.2 represents an
n.sub.2-valent substituent or a linking group, and n.sub.2 is an
integer of 1 to 4. X represents a halogen atom. R.sub.2 and n.sub.2
are respectively the same as those shown in Formula (I), and the
preferable ranges are also the same.
[0032] The raw material carboxylic halide for use is prepared by
acid halogenation of the carboxylic acid compound.
[0033] Examples of the acid halogenating agents for use in
preparation of the carboxylic halide include thionyl chloride,
oxalyl chloride, phosphorus oxychloride, phosphorus trichloride,
phosphorus pentachloride, and the like; favorable examples thereof
include thionyl chloride, oxalyl chloride, and phosphorus
oxychloride; still more preferable are thionyl chloride and oxalyl
chloride; and most preferable is thionyl chloride.
[0034] The solvent for use in preparation of the carboxylic halide
is preferably the solvent used in steps A and B. Particularly
preferable is a non-polar solvent.
[0035] The reaction temperature in preparation of the carboxylic
halide is normally -20 to 100.degree. C., preferably 20 to
90.degree. C., still more preferably 40 to 80.degree. C., still
more preferably 60 to 75.degree. C., and particularly preferably 70
to 73.degree. C.
[0036] As for the ratio of the raw materials in preparation of the
carboxylic halide, the acid halogenating agent is used preferably
in an amount of 0.8 to 5.0 moles, more preferably 1.0 to 3.0 moles,
still more preferably 1.0 to 2.0 moles, still more preferably 1.0
to 1.5 moles, still more preferably 1.0 to 1.3 moles, and most
preferably 1.0 to 1.1 moles, with respect to one carboxyl group of
the carboxylic acid compound.
[0037] The carboxylic halide prepared is preferably supplied as it
is without isolation to the step A. In other words, the reaction
mixture including the carboxylic halide thus prepared is preferably
used in Step A as it is.
[0038] Hereinafter, the step A and the subsequent step will be
described.
[0039] As for the ratio of the raw materials for use in the present
reaction, the n.sub.2-valent carboxylic halide is used preferably
in an amount of 0.3/n.sub.2 to 2.0/n.sub.2 moles, more preferably
0.6/n.sub.2 to 1.5/n.sub.2 moles, and still more preferably
0.8/n.sub.2 to 1.2/n.sub.2 moles, with respect to 1 mole of the
anthranilic acid compound.
[0040] The reaction may be carried out in the presence or absence
of a solvent, preferably in the presence of a solvent. Examples of
the solvents, if used, amide solvents (e.g., N,N-dimethylformamide,
N,N-dimethylacetamide and N-methylpyrrolidinone), sulfone solvent
(e.g., sulfolane), ureide solvents (e.g.,
1-methyl-2-imidazolidinone), urea solvents (e.g., tetramethylurea),
ether solvents (e.g., dioxane and cyclopentylmethylether), ketone
solvents (e.g., acetone, methylethylketone and cyclohexanone),
hydrocarbon solvents (e.g., toluene, xylene and n-decane),
halogenated solvents (e.g., tetrachloroethane and chlorobenzene),
alcohol solvents (e.g., methanol, ethanol, isopropyl alcohol,
ethylene glycol, cyclohexanol and phenol), ester solvents (e.g.,
ethyl acetate and butyl acetate), nitrile solvents (e.g.,
acetonitrile), water, and the like, and these solvents may be used
alone or as a mixture. It is also favorable to add the same or
another solvent in step B after completion of the step A.
[0041] In step A, it is preferred that no protic solvent is used.
Examples of the protic solvent include carboxylic acid series
solvents such as acetic acid, alcoholic solvents such as methanol
and isopropanol, and water. On the contrary, it is preferred that
an aprotic solvent is used in step A. The carboxylic halide used as
the raw material in step A is known to decompose gradually with
protic solvents such as alcohols, and thus, use of a protic solvent
leads to decrease in yield.
[0042] In addition, a solvent having a donor number of 10 or more
is used favorably as the solvent both in steps A and B. The donor
number of solvent is described in detail, for example, in V.
Gutmann, translated by Hitoshi Otaki and Isato Okada, "Donor to
Acceptor: Yoeki.cndot.Hanno no Bunshikan-sogo-sayo (Intermolecular
interaction in solution reaction between donor and acceptor)" 1983,
(Japan Scientific Societies Press) p. 21 to 29. The solvents for
use in the present invention are not limited to those having an
known donor number, as described in these literatures, and thus,
solvents having no known value but seemingly having a value in the
favorable range if determined according to the method described in
literature are also included.
[0043] The donor number of solvent is more preferably 15 or more,
still more preferably 20 or more, and still more preferably 25 or
more. The upper limit of the donor number is not particularly
limited, but it is generally 50, and preferably 40. Examples of the
solvents having a donor number of 15 or more favorably used in the
present invention include ethylene carbonate (DN:16.4, hereinafter
"DN" represents donor number), acetone (DN:17.0), ethyl acetate
(DN:17.1), tetrahydrofuran (DN:20.0), N,N-dimethylformamide
(DN:26.6), N,N-dimethylacetamide (DN:27.8), N-methylpyrrolidinone
(DN:27.3), hexamethylphosphoric triamide (DN:38.8), and the like,
and more preferable are N,N-dimethylformamide,
N,N-dimethylacetamide, and N-methylpyrrolidinone.
[0044] The reaction temperature of step A is normally -50 to
100.degree. C., preferably -40 to 70.degree. C., more preferably
-30 to 50.degree. C., still more preferably -20 to 30.degree. C.,
still more preferably -15 to 20.degree. C., still more preferably
-10 to 10.degree. C., and particularly preferably 0 to 10.degree.
C.
[0045] Alternatively, the reaction temperature of step B is
normally 0 to 200.degree. C., preferably 30 to 180.degree. C.,
still more preferably 50 to 150.degree. C., and particularly
preferably 80 to 130.degree. C.
[0046] In step B, copresence of at least one dehydrating condensing
agent is preferable. Examples of favorable dehydrating condensing
agents include inorganic dehydrating condensing agents (e.g., acid
anhydrides such as sulfuric anhydride and diphosphoric pentoxide
and acid chlorides such as thionyl chloride and phosphorus
oxychloride), organic dehydrating condensing agents (e.g., acid
anhydrides such as acetic anhydride and propionic anhydride, acid
halides such as acetyl chloride, N,N-dicyclohexyl carbodiimide,
etc.), adsorbents such as molecular sieves, and inorganic compounds
incorporating water as crystal solvent such as anhydrous sodium
sulfate. Particularly preferable among them are inorganic and
organic dehydrating condensing agents; still more preferable are
inorganic or organic acid anhydrides; still more preferable are
organic acid anhydrides; and most preferable is acetic
anhydride.
[0047] In the method according to the present invention, a
benzoxazinone-based compound useful as the ultraviolet absorbent
for thermoplastic polymers can be produced inexpensively and
effectively at high purity. Conventional methods, such as the
method described in JP-A-2000-264879, use an alkali and thus had
high possibility of the alkali being contaminated in the final
product, because the intermediate was not isolated. The
contamination of the alkali in the final product is undesirable
from the point of storage life. In contrast, the method according
to the present invention, wherein no alkali is used, does not cause
such a problem.
[0048] The method according to the present invention provides a
benzoxazinone-based compound useful as an ultraviolet absorbent for
thermoplastic polymers inexpensively and effectively at high
purity.
[0049] The present invention will be described in more detail based
on the following examples, but the present invention is not limited
thereto.
EXAMPLES
Example 1
Preparation of Exemplified Compound (I-7)
[0050] 120.7 g of anthranilic acid and 1000 ml of
N-methylpyrrolidinone were placed in a three-necked flask, and the
mixture was dissolved while agitated. 89.3 g of terephthaloyl
chloride (terephthalic dichloride) was added to the solution while
agitated on ice, and the mixture was agitated additionally for 2
hours. The internal temperature was 3 to 8.degree. C. at the time.
Then, 225 g of acetic anhydride and 500 ml of N-methylpyrrolidinone
were added thereto, the mixture was heated while stirred at an
internal temperature of 108 to 116.degree. C. for 2 hours and then
cooled to 30.degree. C. or lower; and the crystal obtained was
filtered and dried, to give 155.6 g of a target exemplified
compound (I-7) (yield: 96%). The content of sodium and potassium in
the exemplified compound obtained (I-7) was 1 ppm or less. The
lower detection limits for sodium and potassium are 1 ppm
respectively, which is applicable to Examples 2 to 8.
[0051] Melting point: 317.3.degree. C.
[0052] Maximum absorption wavelength (.lamda. max) in solution:
349.5 nm (toluene solution)
Example 2
Preparation of Exemplified Compound (I-7)
[0053] 120.7 g of anthranilic acid and 1000 ml of
N,N-dimethylacetamide were placed in a three-necked flask, and the
mixture was dissolved while agitated. 89.3 g of terephthaloyl
chloride was added to the mixture while the mixture was stirred
continuously; the resulting solution was cooled in an ice-methanol
bath; and the mixture was agitated additionally for 1 hour. The
internal temperature was 0 to 5.degree. C. at the time. Then, 225 g
of acetic anhydride and 500 ml of toluene were added thereto; the
mixture was heated and agitated under solvent reflux for 1.5 hours
and then cooled to 30.degree. C. or lower; and the crystal obtained
was filtered and dried, to give 160.5 g of a target exemplified
compound (I-7) (yield: 99%). The content of sodium and potassium in
the exemplified compound obtained (I-7) was 1 ppm or less.
[0054] Melting point: 316.3.degree. C.
[0055] Maximum absorption wavelength (.lamda. max) in solution:
349.5 nm (toluene solution)
Example 3
Preparation of Exemplified Compound (I-7)
[0056] 120.7 g of anthranilic acid and 1000 ml of sulfolane were
placed in a three-necked flask, and the mixture was dissolved while
agitated. 89.3 g of terephthaloyl chloride was added to the
solution while agitated on ice, and the mixture was agitated
additionally for 2 hours. The internal temperature was 6 to
8.degree. C. then. 225 g of acetic anhydride and 500 ml of dioxane
were added thereto, the mixture was heated while agitated under
reflux for 2 hours and then cooled to 30.degree. C. or lower; and
the crystal obtained was filtered and dried, to give 155.6 g of a
target exemplified compound (I-7) (yield: 96%). The content of
sodium and potassium in the exemplified compound obtained (I-7) was
1 ppm or less.
[0057] Melting point: 316.5.degree. C.
[0058] Maximum absorption wavelength (.lamda. max) in solution:
349.5 nm (toluene solution)
Example 4
Preparation of Exemplified Compound (I-8)
[0059] 151.1 g of 2-amino-5-methybenzoic acid and 1200 ml of
N,N-dimethylacetamide were placed in a three-necked flask, and the
mixture was dissolved while agitated. 101.5 g of terephthaloyl
chloride was added to the mixture while the mixture was stirred
continuously; the resulting solution was cooled in an ice-methanol
bath; and the mixture was agitated additionally for 2 hours. The
internal temperature was -3 to 4.degree. C. at the time. Then, 254
g of acetic anhydride and 600 ml of toluene were added thereto; the
mixture was heated and agitated under solvent reflux for 1.5 hours
and then cooled to 30.degree. C. or lower; and the crystal obtained
was filtered and dried, to give 194.2 g of a target exemplified
compound (I-8) (yield: 98%). The content of sodium and potassium in
the exemplified compound obtained (I-8) was 1 ppm or less.
Example 5
Preparation of Exemplified Compound (I-13)
[0060] 171.6 g of 2-amino-5-chlorobenzoic acid and 1400 ml of
N,N-dimethylacetamide were placed in a three-necked flask, and the
mixture was dissolved while agitated. 101.5 g of terephthaloyl
chloride was added to the solution while agitated on ice, and the
mixture was agitated additionally for 4 hours. The internal
temperature was 4 to 11.degree. C. then. 254 g of acetic anhydride
and 600 ml of N-dimethylacetamide were then added thereto; the
mixture was heated while stirred at an internal temperature of 105
to 126.degree. C. for 2 hours, and then, cooled to 30.degree. C. or
lower; and the crystal obtained was filtered and dried, to give
212.1 g of a target exemplified compound (I-13) (yield: 97%). The
content of sodium and potassium in the exemplified compound (I-13)
obtained was 1 ppm or less.
Example 6
Preparation of Exemplified Compound (I-6)
[0061] 13.7 g of anthranilic acid and 100 ml of
N,N-dimethylacetamide were placed in a three-necked flask, and the
mixture was dissolved while agitated. 14.7 g of 2-thiophene
carbonyl chloride was added to the solution while agitated on ice,
and the mixture was agitated additionally for 4 hours. The internal
temperature was 7 to 13.degree. C. then. 25 g of acetic anhydride
and 50 ml of N,N-dimethylacetamide were then added thereto; the
mixture was heated while stirred at an internal temperature of 98
to 118.degree. C. for 2 hours, and then, cooled to 30.degree. C. or
lower; and the crystal obtained was filtered and dried, to give
21.8 g of a target exemplified compound (I-6) (yield: 95%). The
content of sodium and potassium in the exemplified compound (I-6)
obtained was 1 ppm or less.
Example 7
Preparation of Exemplified Compound (I-7)
[0062] 73.1 g of terephthalic acid and 280 ml of toluene were
placed in a three-necked flask, and the mixture was agitated while
cooled on ice. 157.1 g of thionyl chloride was added dropwise
thereto; the mixture was heated while agitated at an internal
temperature of 50 to 75.degree. C. for 7 hours, and then cooled to
30.degree. C. or lower. 280 ml of water was added thereto; the
mixture was agitated for 5 minutes; and then the aqueous phase was
removed. It was added to a mixture of 120.7 g of anthranilic acid
and 1000 ml of N,N-dimethylacetamide placed in a three-necked flask
that was previously dissolved by agitation and agitated
continuously as cooled in an ice-methanol bath, and the resulting
mixture was stirred additionally for 1 hour. The internal
temperature was 0 to 5.degree. C. at the time. Then, 225 g of
acetic anhydride and 220 ml of toluene were added thereto; the
mixture was agitated and heated under solvent reflux for 1.5 hours
and then cooled to 30.degree. C. or lower; and the resulting
crystal was filtered and dried, to give 160.5 g of a target
exemplified compound (I-7) (yield: 96%). The content of sodium and
potassium in the exemplified compound (I-7) obtained was 1 ppm or
less.
Example 8
Preparation of Exemplified Compound (I-8)
[0063] 83.1 g of terephthalic acid and 300 ml of toluene were
placed in a three-necked flask, and the mixture was agitated while
cooled on ice. 178.5 g of thionyl chloride was added dropwise
thereto; the mixture was heated while agitated at an internal
temperature of 50 to 75.degree. C. for 7 hours, and then cooled to
30.degree. C. or lower. 420 ml of water was added thereto; the
mixture was agitated for 5 minutes; and then the aqueous phase was
removed. It was added to a mixture of 151.1 g of
2-amino-5-methybenzoic acid and 1200 ml of N,N-dimethylacetamide
placed in a three-necked flask that was previously dissolved by
agitation and agitated continuously as cooled in an ice-methanol
bath, and the resulting mixture was stirred additionally for 2
hours. The internal temperature was 0 to 5.degree. C. then. Then,
254 g of acetic anhydride and 300 ml of toluene were added thereto;
the mixture was agitated and heated under solvent reflux for 1.5
hours and then cooled to 30.degree. C. or lower; and the resulting
crystal was filtered and dried, to give 194.2 g of a target
exemplified compound (I-8) (yield: 98%). The content of sodium and
potassium in the exemplified compound (I-8) obtained was 1 ppm or
less.
<Evaluation>
(Preparation of Ultraviolet-Absorbing Filter)
[0064] 150 ml of chloroform was added to 10 g of polymethyl
methacrylate (PMMA) and 0.1 g of the compound represented by
Formula (I) shown in Table 1, and the mixture was agitated and
dissolved at 40.degree. C. for 60 minutes; the resulting solution
was coated on a glass plate and air-dried at room temperature, to
give an ultraviolet-absorbing filter sample. As shown in Table 1,
the compound represented by Formula (I) was prepared as a
Comparative Example, according to the method described in Example 2
of U.S. Pat. No. 3,408,326 or the method described in Example 1 of
JP-A-2000-264879.
(Light Fastness Test)
[0065] The sample obtained was exposed to the light from a xenon
lamp at an intensity of 170,000 lux for 3 days, the intensities of
the absorption at the maximum spectroscopic absorption wavelength
of the compound represented by Formula (I) before and after
irradiation were determined, and the light fastness was calculated
based on the retention rate. Results are summarized in Table 1.
TABLE-US-00001 TABLE 1 Sample Exemplified Concentration of Light
No. Compound No. sodium in product Fastness Remarks 1 (I-7) 1 ppm
or less 98 Isolated product of Example 1 This invention of the
present invention 2 (I-7) 1 ppm or less 99 Isolated product of
Example 2 This invention of the present invention 3 (I-7) 1 ppm or
less 98 Isolated product of Example 3 This invention of the present
invention 4 (I-8) 1 ppm or less 98 Isolated product of Example 4
This invention of the present invention 5 (I-13) 1 ppm or less 97
Isolated product of Example 5 This invention of the present
invention 6 (I-7) 35 ppm 88 Prepared by the method of Example 2
Comparative of U.S. Pat. No. 3,408,326 example 7 (I-7) 360 ppm 79
Prepared by the method of Example 1 Comparative of JP-A-2000-264879
example 8 (I-8) 430 ppm 85 Prepared by the method of Example 1
Comparative of JP-A-2000-264879 example 9 (I-13) 460 ppm 80
Prepared by the method of Example 1 Comparative of JP-A-2000-264879
example
[0066] As obvious from the results shown in Table 1, the compounds
represented by Formula (I) prepared by the method according to the
present invention were higher in purity and light fastness than the
compounds prepared by other preparative methods.
INDUSTRIAL APPLICABILITY
[0067] According to the present invention, a benzoxazinone-based
compound useful as the ultraviolet absorbent for thermoplastic
polymers can be produced inexpensively and effectively at high
purity. The benzoxazinone-based compound produced by the present
invention method can provide an ultraviolet absorbing material with
high-purity and light fastness useful in optical film
application.
[0068] Having described our invention as related to the present
embodiments, it is our intention that the invention not be limited
by any of the details of the description, unless otherwise
specified, but rather be construed broadly within its spirit and
scope as set out in the accompanying claims.
[0069] This non-provisional application claims priority under 35
U.S.C. .sctn.119 (a) on Patent Application No. 2007-252729 filed in
Japan on Sep. 27, 2007, and Patent Application No. 2008-091834
filed in Japan on Mar. 31, 2008, each of which is entirely herein
incorporated by reference.
* * * * *